US3328452A - Thiosulfoalkanoate compounds - Google Patents
Thiosulfoalkanoate compounds Download PDFInfo
- Publication number
- US3328452A US3328452A US483361A US48336165A US3328452A US 3328452 A US3328452 A US 3328452A US 483361 A US483361 A US 483361A US 48336165 A US48336165 A US 48336165A US 3328452 A US3328452 A US 3328452A
- Authority
- US
- United States
- Prior art keywords
- compounds
- acid
- urease
- thiosulfoalkanoate
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 title claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 108010046334 Urease Proteins 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- YYSCJLLOWOUSHH-UHFFFAOYSA-N 4,4'-disulfanyldibutanoic acid Chemical compound OC(=O)CCCSSCCCC(O)=O YYSCJLLOWOUSHH-UHFFFAOYSA-N 0.000 description 2
- WRWNIAIJFOMJBL-UHFFFAOYSA-N 4-hydroxysulfonothioylbutanoic acid Chemical compound OC(=O)CCCS(O)(=O)=S WRWNIAIJFOMJBL-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DZHMRSPXDUUJER-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;dihydrogen phosphate Chemical compound NC(N)=O.OP(O)(O)=O DZHMRSPXDUUJER-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- UTDRPUGFHHVEDG-UHFFFAOYSA-N 2-(1-carboxylatoethyldisulfanyl)propanoate;hydron Chemical compound OC(=O)C(C)SSC(C)C(O)=O UTDRPUGFHHVEDG-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- DTRIDVOOPAQEEL-UHFFFAOYSA-N 4-sulfanylbutanoic acid Chemical compound OC(=O)CCCS DTRIDVOOPAQEEL-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101000808346 Canavalia ensiformis Urease Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical class [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/04—Thiosulfonates
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
- A23K50/15—Feeding-stuffs specially adapted for particular animals for ruminants containing substances which are metabolically converted to proteins, e.g. ammonium salts or urea
Definitions
- novel chemical compounds of the invention are S-2-carboxyethyl 3-thiosulfopropionate and S-3-carboxypropyl 4-thiosulfobutyrate which can "be represented by the structural formula H000 (C Z)ni S (CH2) CODE Where n represents 2 and 3 respectively.
- the compounds can be named 3,3'-dithiodipropionic acid S,S- dioxide and 4,4'-dithiodibutyric acid S,S-dioxide.
- the compounds have valuable properties as inhibitors of the enzyme urease which hydrolyzes urea to ammonia and carbon dioxide, and thus are useful for the control of ammonia production and for the improvement of feed utilization in domestic animal rations.
- the new compounds of the invention are obtained in one method by the oxidation of 3-mercaptopropionic acid or 4-mercaptobutyric acid with aqueous hydrogen peroxide in an acidic medium at 3050 C. or with a per acid as for example, peracetic or perbenzoic acid in an inert solvent, for example chloroform, ethyl acetate, etc., at temperatures between 0 C. and 40 C.
- a per acid as for example, peracetic or perbenzoic acid in an inert solvent, for example chloroform, ethyl acetate, etc.
- the appropriate mercaptoalkanoic acid is dissolved in glacial acetic acid and oxidized with aqueous hydrogen peroxide at a temperature between 35- 40 C.
- Use of substantially higher temperatures results in markedly decreased yields and contamination with products at higher stages of oxidation.
- EXAMPLE -1 S-Z-carboxyethyl 3-thioswlf0pr0pionate To a solution of 530 g. of 3-mercaptopropionic acid in 500 ml. of glacial acetic acid was added dropwise 1020 ml. of 30% aqueous hydrogen peroxide. The addition required four hours, during which time the temperature of the reaction mixture was kept below 40 C. by occasional use of a cooling bath. After the addition was completed the mixture was stirred for three hours at 3538 C. then left overnight in the refrigerator. The solid which separated was collected by filtration, taken up in 600 ml. of water and the slurry made basic with 120 g. of sodium carbonate.
- EXAMPLE 2 S-3-carb0xypropyl 4-thi0sulfobulyrate To a suspension of 23.8 g. of 4,4'-dithiodibutyric acid in 50 ml. of glacial acetic acid was added dropwise 25 ml. of 30% aqueous hydrogen peroxide. The temperature of the reaction mixture was kept between 37 C. and 41 C. during the one and one-half hours required for the addition. After the addition was complete the temperature was held at 4143 C. for three hours. The reaction mixture was cooled and then left standing overnight. The acetic acid was removed by vacuum distillation and the wax-like white solid residue slurried in 50 ml. of ether and then recovered by filtration.
- the S-2-carboxyethyl 3-thiosulfopropionate and 8-3- carboxypropyl 4-thiosulfobutyrate react with inorganic and organic bases to form the corresponding monoor di salts, depending on whether one or two equivalents of base are employed and are the full equivalent of the subject matter specifically claimed.
- the water-soluble alkali metal salts and the ammonium salts are especially useful and economical forms for many purposes, but other salts are also readily obtained and may be preferred in some instances, for example: the alkaline earth metal salts, for instance the calcium, magnesium and barium salts; the copper, mercury and arsenic salts; and substituted ammonium salts, for instance the dimethylammonium and triethanolammonium salts.
- the above compounds inhibit urease in vitro.
- the inhibition can be readily determined by means of standard biological test procedures. For instance, the following method is used.
- One ml. of a urease solution containing 1.5 mg. of crystalline jack bean urease is pipetted into a prewarmed test tube.
- One ml. of water, in the case of control determinations, or a 1 ml. aqueous solution of test agent is added to the urease solution, mixed and allowed to preincubate for five minutes.
- Reaction is initiated by rapid addition of 1 ml. of urea-phosphate solution to the enzyme-test agent mixture.
- the ureaphosphate solution consists of 3% urea containing 9.6% phosphate buffered at a final pH of 7.0.
- the new compounds can be employed to increase feed utilization in animal rations by conventional methods, for instance, by incorporation in bulk feeds at levels of 5-100 g. P61 IOII.
- n 2 or 3.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,328,452 THIOSULFOALKANOAT E COMPOUNDS William B. Dickinson, Loudonville, N.Y., assignor to Sterling Drug Inc., New York, N.Y., a corporation of Delaware No Drawing. Filed Aug. 27, 1965, Ser. No. 483,361 3 Claims. (Cl. 260-453) This invention relates to chemical compositions of matter classified as thiosulfoalkanoates.
The novel chemical compounds of the invention are S-2-carboxyethyl 3-thiosulfopropionate and S-3-carboxypropyl 4-thiosulfobutyrate which can "be represented by the structural formula H000 (C Z)ni S (CH2) CODE Where n represents 2 and 3 respectively. Alternatively the compounds can be named 3,3'-dithiodipropionic acid S,S- dioxide and 4,4'-dithiodibutyric acid S,S-dioxide.
The compounds have valuable properties as inhibitors of the enzyme urease which hydrolyzes urea to ammonia and carbon dioxide, and thus are useful for the control of ammonia production and for the improvement of feed utilization in domestic animal rations.
The new compounds of the invention are obtained in one method by the oxidation of 3-mercaptopropionic acid or 4-mercaptobutyric acid with aqueous hydrogen peroxide in an acidic medium at 3050 C. or with a per acid as for example, peracetic or perbenzoic acid in an inert solvent, for example chloroform, ethyl acetate, etc., at temperatures between 0 C. and 40 C. In a second method for the preparation of the compounds the corresponding dithiodialkanoic acids are oxidized with hydrogen peroxide in an acidic medium or a peracid in an inert solvent at temperatures between 30 C. and 50 C. In the preferred method the appropriate mercaptoalkanoic acid is dissolved in glacial acetic acid and oxidized with aqueous hydrogen peroxide at a temperature between 35- 40 C. Use of substantially higher temperatures results in markedly decreased yields and contamination with products at higher stages of oxidation.
The invention is illustrated by the following examples without, however, being limited thereto.
EXAMPLE -1 S-Z-carboxyethyl 3-thioswlf0pr0pionate To a solution of 530 g. of 3-mercaptopropionic acid in 500 ml. of glacial acetic acid was added dropwise 1020 ml. of 30% aqueous hydrogen peroxide. The addition required four hours, during which time the temperature of the reaction mixture was kept below 40 C. by occasional use of a cooling bath. After the addition was completed the mixture was stirred for three hours at 3538 C. then left overnight in the refrigerator. The solid which separated was collected by filtration, taken up in 600 ml. of water and the slurry made basic with 120 g. of sodium carbonate. The resultant solution was filtered, the filtrate acidified with 205 ml. of concentrated hydrochloric acid in 400 ml. of Water and the mixture refrigerated. The solid which separated was collected by filtration and dried in a vacuum oven at 60 C. Several recrystallizations from water gave 339 g. of S-Z-carboxyethyl 3-thiosulfopropiouate having the molecular formula C H O S and melting at l46-'147 C. with decomposition.
EXAMPLE 2 S-3-carb0xypropyl 4-thi0sulfobulyrate To a suspension of 23.8 g. of 4,4'-dithiodibutyric acid in 50 ml. of glacial acetic acid was added dropwise 25 ml. of 30% aqueous hydrogen peroxide. The temperature of the reaction mixture was kept between 37 C. and 41 C. during the one and one-half hours required for the addition. After the addition was complete the temperature was held at 4143 C. for three hours. The reaction mixture was cooled and then left standing overnight. The acetic acid was removed by vacuum distillation and the wax-like white solid residue slurried in 50 ml. of ether and then recovered by filtration. Recrystallization from 1,750 ml. of ether followed by drying at 40 C. in vacuo gave 6.2 g. of S-3-carboxypropyl 4-thiosulfobutyrate having the molecular formula C H O S and melting at 97103 C.
The S-2-carboxyethyl 3-thiosulfopropionate and 8-3- carboxypropyl 4-thiosulfobutyrate react with inorganic and organic bases to form the corresponding monoor di salts, depending on whether one or two equivalents of base are employed and are the full equivalent of the subject matter specifically claimed. The water-soluble alkali metal salts and the ammonium salts are especially useful and economical forms for many purposes, but other salts are also readily obtained and may be preferred in some instances, for example: the alkaline earth metal salts, for instance the calcium, magnesium and barium salts; the copper, mercury and arsenic salts; and substituted ammonium salts, for instance the dimethylammonium and triethanolammonium salts.
The structural formulas assigned to the products of the invention are in full conformance with the modes of synthesis employed in obtaining them and with the results of elementary and spectral analyses of the products.
The above compounds inhibit urease in vitro. The inhibition can be readily determined by means of standard biological test procedures. For instance, the following method is used. One ml. of a urease solution containing 1.5 mg. of crystalline jack bean urease is pipetted into a prewarmed test tube. One ml. of water, in the case of control determinations, or a 1 ml. aqueous solution of test agent is added to the urease solution, mixed and allowed to preincubate for five minutes. Reaction is initiated by rapid addition of 1 ml. of urea-phosphate solution to the enzyme-test agent mixture. The ureaphosphate solution consists of 3% urea containing 9.6% phosphate buffered at a final pH of 7.0. After five minutes of reaction time, 1 ml. of l/=l (v./v.) sulfuric acid is added. The contents of the test tubes are rinsed thoroughly into 200 ml. volumetric flasks, filled to within 50 ml. of the mark and 10 ml. of 10% sodium hydroxide added. The ammonia released by urease action is developed colorimetrically by the rapid addition of 15 ml. of Nesslers reagent. The flasks are made up to 200 ml. with water and read after fifteen minutes in an Evelyn color-imeter at 520 mg. The ammonia produced by urease is compared with controls on a Standard curve of optical density vs. mg. of ammonia nitrogen. Thus using this procedure S-Z-carboxyethyl 3- thiosulfopro'pionate inhibited urease by 50% at 4.3 10- M and S-3-carboxypropyl 4-thiosulfo'butyrate at 3.5 X 10 M. In contrast the known 2,2-dithiodipropionic acid and S-carboxymethyl thiosulfinoacetate gave 4% inhibition at l 10- M and 5X l0 M respectively.
The new compounds can be employed to increase feed utilization in animal rations by conventional methods, for instance, by incorporation in bulk feeds at levels of 5-100 g. P61 IOII.
3 4 I claim: 2. S-Z-carboxyethyl 3-thiosu1fopropionate. 1. A compound of the formula 3. S-3-carboxypropy1 4-thiosu1fobutyrate.
No references cited. HOOC(OHz)DSS(CHz)uCOOH 5 3 CHARLES E. PARKER, Primary Examiner.
Where n is 2 or 3. JOSEPH P. BRUST, Examiner.
Claims (1)
1. A COMPOUND OF THE FORMULA
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US483361A US3328452A (en) | 1965-08-27 | 1965-08-27 | Thiosulfoalkanoate compounds |
| GB35912/66A GB1107529A (en) | 1965-08-27 | 1966-08-10 | Thiosulphoalkanoates |
| FR73696A FR1500967A (en) | 1965-08-27 | 1966-08-22 | New thiosulfoalkanoates and their preparation process |
| DEST25799A DE1287069B (en) | 1965-08-27 | 1966-08-24 | Process for the preparation of Thiosulfonalkylcarbonsaeurederivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US483361A US3328452A (en) | 1965-08-27 | 1965-08-27 | Thiosulfoalkanoate compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3328452A true US3328452A (en) | 1967-06-27 |
Family
ID=23919755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US483361A Expired - Lifetime US3328452A (en) | 1965-08-27 | 1965-08-27 | Thiosulfoalkanoate compounds |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3328452A (en) |
| DE (1) | DE1287069B (en) |
| FR (1) | FR1500967A (en) |
| GB (1) | GB1107529A (en) |
-
1965
- 1965-08-27 US US483361A patent/US3328452A/en not_active Expired - Lifetime
-
1966
- 1966-08-10 GB GB35912/66A patent/GB1107529A/en not_active Expired
- 1966-08-22 FR FR73696A patent/FR1500967A/en not_active Expired
- 1966-08-24 DE DEST25799A patent/DE1287069B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1287069B (en) | 1969-01-16 |
| GB1107529A (en) | 1968-03-27 |
| FR1500967A (en) | 1967-11-10 |
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